(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

Base Information

Chemical Name:(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one
CAS No.:1395342-29-6
Molecular Formula:C₂₀H₂₀BrNO₂S₂
Molecular Weight:450.42
Hs Code.:

Synonyms:(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

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Chemical Property of (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

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Technology Process of (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

There total 1 articles about (2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 1122-91-4
4-bromo-benzaldehyde

: 263764-23-4,863324-53-2
(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione

: 1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

: 1395342-29-6
(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

Guidance literature:: (S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.416667h; Inert atmosphere;

With (-)-sparteine; In dichloromethane; at 0 ℃; for 0.333333h; Inert atmosphere;

4-bromo-benzaldehyde; optical yield given as %de; stereoselective reaction; Further stages;
DOI:10.1055/s-0031-1290670

Reference yield: 96.7%

: 1395342-29-6
(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 1395342-57-0
(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-2-methyl-3-((triethylsilyl)oxy)propan-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; Inert atmosphere;
DOI:10.1055/s-0031-1290670

Reference yield:

: 1395342-29-6
(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(4-bromophenyl)-3-hydroxy-2-methylpropan-1-one

: 1395342-38-7
(2R,3R,9R,10S,E)-3-allyl-2,10-bis((triethylsilyl)oxy)-9-methyl-10-(4-bromophenyl)-decane-6-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-dimethylpyridine / dichloromethane / -78 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

3.1: tetrahydrofuran / 20 °C / Inert atmosphere; Reflux

4.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / 5 h / Inert atmosphere; Reflux

5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

6.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6.2: 20 °C / Inert atmosphere

7.1: N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; methyllithium; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -50 °C / Inert atmosphere

7.2: 1 h / -50 °C / Inert atmosphere

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; methyllithium; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid hydrazide; barium(II) hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; 3.1: Wittig reaction / 5.2: Claisen condensation / 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1290670